ClickUp

I lead ClickUp’s content-led social strategy, generating 200 million impressions per month and turning viral reach into high-performing ads that lower CAC payback.

What I Run & Manage:

Organic Social Growth – Creating viral, high-impact content that drives awareness and engagement.

Paid Amplification – Transforming top-performing organic content into ads that convert.

Social Media Team – Leading a world-class team of creatives, strategists, and editors.

Platform Strategy – Optimizing content for TikTok, Instagram, YouTube, LinkedIn, and Facebook.

Performance & Analytics – Measuring impact, refining strategies, and scaling what works.

By blending organic storytelling with paid distribution, I maximize impact across platforms—driving brand awareness, engagement, and revenue. My focus is on content that stops the scroll, sparks conversations, and scales growth.

(Founding Member) Marketing 

As Head of Influencer Marketing, I'm responsible for:

- Finding creators who best represent ClickUp 
- Growing long term meaningful relationships with Thought Leaders
- Creating content for social media and ads
- Driving new users to the platform via social media
- Empowering creators to use ClickUp
- Discovering new creative ways to show off our platform

Head of Influencer Marketing / Founding Member

At ClickUp, I'm responsible for: 

-Driving high quality, high performing, engaging and innovative marketing while also contributing to overall agency thought leadership
-Managing and growing Partnerships with other companies
-Driving organization-wide social media efforts, stay on the leading edge of trends and technologies and advocate for new approaches that advance the department and its goals.
-Find ways to further enhance the branding of a ClickUp, as well as develop a marketing plan through analysis of current market data and trends.
-And most importantly, make shit go viral

Senior Brand Strategist/Founding Member

Clickup is a privately held project management application service provider based in Palo Alto, California. Clickup's primary product is an online tool for project management and work collaboration.

This role's main responsibilities include:

-Increase renewal rates and reduce churn
-Expand revenue in accounts through cross-sell and up-sell
-Influence future lifetime value through higher product adoption, customer satisfaction, and overall health scores
-Drive new business growth through greater advocacy and reference-ability
-Define operational metrics for team
-Establish system for tracking metrics
-Drive company-wide definition of ideal customer

Chris will still manage the Enterprise Sales Team focused on providing customer experience solutions to companies with revenues greater than 5 Million as well as the client success team who helps these customers.

Vice President of Sales/Customer Success

Clickup is a privately held project management application service provider based in Palo Alto, California. Clickup's primary product is an online tool for project management and work collaboration.

Chris is tasked with growing the Enterprise Sales Team focused on providing customer experience solutions to companies with revenues greater than 5 Million. He continues to speak to all of our high profile clients while also growing our entire sales/internship teams. As a senior management team member reporting directly to the CEO, he is responsible for the success of our sales team members as measured by revenue and new sales bookings.

Vice President of Sales

Mango Technologies, Inc

Mango Technologies, Inc  provides software solutions that drive better customer experiences while reducing operational costs. Mango Technologies, Inc is the parent company for both ClickUp and Mimri.

I was is tasked with growing the Enterprise Sales Team focused on providing customer experience solutions to companies with revenues greater than 5 Million. I spoke to all of our high profile clients while also growing the entire sales/internship teams. As a senior management team member reporting directly to the CEO, I was responsible for the success of our sales team members as measured by revenue and new sales bookings.

Head Of Business Development

Cvent

• Mentor a team of new and experienced sales professionals to achieve and surpass individual and department goals.
• Coach, mentor, provide feedback and improve the skill set and productivity of the team.
• Identify, innovate and execute business ideas to improve division goals and targets.
• Initiate, manage, take ownership of strategic dialogues with other teams, including Marketing, Technology, Client Services and other division heads.
• Facilitate on-boarding and training for new associates.
• Assisting in implementation of strategic goals and tactical planning for our sales organization.

Team Lead, Sales Development

I monitor Cvent's premiere meeting planner clients and many more to ensure return on investment and customer satisfaction. I assist with specific projects and trainings for the team, while assigning work to the other employees on the Escalation Team.

Senior Sales Associate, Client Success

I help clients to understand how to use our software. I reach out to clients and assist them in using our software. If I see a fit for marketing, I pass these clients on to the proper sales contact. I help clients get set up for trainings or edit their profile etc.

Sales Associate, Cvent Supplier Network

Beverly Media

Managed Social media for Influencers. Helped them grow social and link with brands for promotion. Managed actors, professional athletes, and many other high profile clients.

Eventually linked with Spin Social to offer analytics and automated posting. Exited the company in 2014 and both were bought out!

Manager of Business Development

SPIN Social Media

Ran analytics and automated posting for clients social media. Sold the technology to Hootsuite and closed the company.

Business Development

Verizon Wireless

Sold all Verizon products while opening and closing the store. Worked off hourly pay plus commission.

Sales Manager

College Media Solutions

Sold advertising for Virginia Tech through the Collegiate Times and VT network.
Took care of a client list and made sure they were always pleased.  Worked off commission by ads sold.

Account Executive

People person from a small town. Working hard to better myself everyday and will take on every project I have time for.

CMO: "I want to spend $200K on TikTok creators."

CEO: "TikTok? Our buyers are 45-year-old VPs, not teenagers."

CMO: "That's exactly why it'll work."

CEO: "Explain."

CMO: "Everyone thinks B2B buyers live on LinkedIn 24/7. But Sarah, your VP of Sales? She's scrolling TikTok at 9 PM after her kids go to bed."

CEO: "So?"

CMO: "So when she sees our content explaining the exact problem she dealt with that day, we're not just another vendor. We're the company that 'gets it.'"

CEO: "But can we track ROI?"

CMO: "Wrong question. Can we track when someone sees our Super Bowl ad then buys 6 months later? No. But we still run Super Bowl ads."

CEO: "This is different."

CMO: "It's not. Here's what'll happen: Sarah sees our video about project management nightmares. Doesn't remember our name. Three months later, her current tool breaks. She Googles 'project management software' and recognizes our logo. Clicks us first."

CEO: "That's.. actually smart."

CMO: "Plus, our sales team will start hearing 'we've seen your content' on calls. Trust me, I've been tracking this at my last three companies."

CEO: "Fine. But if this doesn't work.."

CMO: "If it doesn't work, I'll go back to boring LinkedIn carousels."

CEO: "Deal."

6 months later, that CMO became the highest-paid marketing exec in their industry.

Sometimes the craziest ideas are the smartest ones.

I'm Chris Cunningham, I run social media at ClickUp.

Follow me for more B2B marketing content as I build this all in public, right here on LinkedIn.

Chris  Cunningham

I have no idea which TikTok drove our biggest deal last quarter.
And honestly? I don't care.
Top of Funnel attribution is dumb.

👇 Here's why you're measuring B2B social media completely wrong:

We're generating 200 million impressions a month at ClickUp.

So I get it..
 
But you're obsessed with attribution that doesn't actually matter.
 
Every CMO wants to draw a straight line from post to pipeline.
Every CFO wants to see direct ROI from that viral video.
Every Board Member asks "but how many leads did it generate?"

Wrong questions.

👇 Here's what actually happens

(1) Prospect sees your content 6 months ago.
(2) Forgets about it.
(3) Runs into the problem you solve.
(4) Remembers "that company with the funny videos."
(5) Googles you.
(6) Books a demo.

Your CRM says it was "organic search."

But it wasn't.

It was that TikTok they can't even remember watching.

What I actually measure:

• Are sales reps hearing about our content on calls?
• Are competitors starting to copy our style?
• Are people applying to work here because of our videos?
• Are industry analysts mentioning our content?

Those are leading indicators.
Revenue is a lagging indicator.

PROBLEM

Most B2B brands will spend $50K on a trade show booth and never question ROI.

But they'll scrutinize every dollar on content creation.

That's backwards.

👇 My advice?

Start with impressions from your ideal customers.
Layer in attribution later.
Don't let perfect tracking kill good content.

The brands winning on social aren't the ones with the best dashboards.

They're the ones people actually want to follow.

Build that first.

Everything else will follow.

Thoughts?

I'm Chris Cunningham, I run Social Media marketing at ClickUp.

Follow me for more as I build this content machine in public on LinkedIn.

Sh*t, it's my birthday.

5 devastating mistakes I made (and will never make again).

The crazy part? I learned every single lesson from my best friends.

→ Stop overthinking and just dive in
→ Align every decision with your purpose
→ Make fear your friend, not your enemy
→ Breathe before you react
→ Always show up for the people you love

Look, I could've made this some polished corporate birthday post about "another year of growth" or whatever.

But that's not real.

Real growth comes from owning your mistakes and learning from the people who call you out on them.

Shoutout to everyone mentioned in this video - you've shaped who I am today.

The only birthday gift I want?

Take these lessons and live an extraordinary life.

PS - I actually just turned 36, and this video is from 2 years ago. But honestly? These lessons hit just as hard, if not even harder now.

"First ad that actually made me want to try ClickUp"

This is crazy. My YouTube ad is getting more attention than our TikToks.

And our TikToks have 200+ million views..

It's titled, "My Work is Easy Because I Use ClickUp"

I'm getting 3-5 messages a day from people saying:

"Dude, your YT ad is everywhere."
"This ad doesn't feel like an ad"
"You look like you need coffee but I signed up anyway."

No HR guys dancing to 2000s hits.
No trending audio.
No fancy editing.

Just me walking through how I actually organize my tasks.

People are literally reaching out to connect on LinkedIn because of a 30-second screen recording where I explain my workflow.

I think I accidentally figured something out..

Why do you think this is working so well?

Desktop view of a viral YouTube ad about ClickUp

Marketers - I need your help to take ClickUp to 300M+ monthly impressions.
 
What would you do in my position? Share your ideas below 👇
 
BACKGROUND
 
Last year we hit 200M+ monthly impressions across all our social media channels.
 
Now, they want me to hit 300M+, and I know they'll want even more after that.
 
What would YOU do in my position?
 
I'm thinking:
 
(1) Double down on micro-influencers (the HR skits are working, but we need more angles)
 
(2) Revamp our YouTube strategy (our short-form is crushing it, but our long-form needs work)
 
(3) Create more middle-funnel product content (everyone knows ClickUp exists now - we need content that makes you want to USE us)
 
Drop your most tactical, specific idea below.
 
Not looking for "post more reels" advice - give me something I haven't thought of.
 
Let's see what you got!

ClickUp Social Media iMessage between Chris, Zeb, and Gaurav.

Everyone says "play to your strengths." I say attack your weaknesses instead.

I used to stutter as a kid because I'd speak so fast. Now I speak from stage all over the world.

BACKGROUND
 
I've always thought speaking on stage was the most badass thing you could do.
 
Then I completely bombed my first opportunity.
 
I'm talking full meltdown.
 
Forgot my points, stumbled over words, and wanted to crawl under the podium.
 
Instead of letting that break me, I chose to turn that weakness into a strength.
 
Started taking Toastmasters classes.
 
Said yes to every speaking opportunity, no matter how small.
 
Practiced in mirrors, recorded myself, and slowly figured out what worked.
 
Fast forward to today:
 
I'm crushing stages at conferences, sharing ClickUp's story, and actually loving every minute of it.
 
TAKEAWAY
 
Your biggest failures often become your greatest strengths.
 
But only if you're willing to do the work.
 
Thoughts?

I asked ChatGPT why most B2B social media content fails. And honestly? Its 7-point answer was really good.
Even AI understands this stuff better than most companies.

👇 Here's what ChatGPT had to say:

(1) ➝ Talking to Themselves, Not Their Audience

Many B2B companies fall into the trap of writing for their peers or competitors rather than their actual buyers.

The content ends up stuffed with jargon, acronyms, and internal lingo that only insiders care about.

This creates a disconnect from the real-world problems and language their target audience uses.

(2) ➝ Fear of Personality

There's often a deep-rooted fear of sounding “unprofessional,” which leads to sterile, safe, and boring content.

But in reality, personality is professional when done right.

Buyers are still humans. Even in enterprise sales, and they connect with authenticity, humor, and boldness.

(3) ➝ Content By Committee

Large content teams or marketing departments often dilute ideas through rounds of approvals, edits, and risk-averse stakeholders.

By the time content gets published, it’s a shadow of the original idea.

No punch, no edge – just corporate mush.

(4) ➝ Lack of POV (Point of View)

Great content has a clear stance. Most B2B content tries to please everyone and ends up saying nothing.

Engaging content often has a contrarian take, a strong opinion, or a bold prediction.

Most B2B teams avoid this because they don't want to rock the boat.

(5) ➝ Misalignment Between Sales and Marketing

Marketing may not be talking to customers as much as the sales team is.

Without that frontline intel – the exact objections, pain points, and language customers use – content ends up missing the mark.

It becomes more about features than outcomes.

(6) ➝ Overthinking SEO and Under-thinking Value

Chasing search volume and keywords too mechanically leads to robotic content.

B2B teams often prioritize rankings over resonance.

Real value comes from insight, storytelling, and usefulness – not just keyword density.

(7) ➝ No System for Content Creation

B2B companies often don’t have a repeatable system to generate, test, and repurpose content across platforms.

Without a clear strategy, content becomes random acts of marketing rather than a flywheel.

Thoughts?

ChatGPT question about why most B2B companies struggle to create engaging content.

Watch this. Then read below. 👇
I need your help crowdsourcing the most cringe-worthy corporate speak for our next skit.

The more painful, the better.

Drop your favorites below 👇

PS - I'm Chris Cunningham and I run social media at ClickUp

Follow me for how we come up with our best social strategies (and all the failures in between).

"B2B companies shouldn't act like B2C brands" - this is total BS
 
3 ways B2B marketing is stealing from B2C in 2025:
 
(1) Instagram behind-the-scenes content → Show the humans building your product → Makes AI-obsessed buyers trust you're real

(2) TikTok educational series → 60-second expert tips → Repurpose everywhere (LinkedIn loves this)

(3) Influencer partnerships that don't suck → Find creators who actually use your product → No fake testimonials (people smell BS instantly)
 
Everyone thinks B2B marketing has to be buttoned-up and boring.
 
That's exactly why your competitors are losing (and where your brand can stand out).
 
• Your ICP scrolls TikTok at 2am
• They're on Instagram during meetings
• They're humans first, buyers second

🛑 Stop creating content for corporate robots.
✔️ Start creating for the person behind the title.
 
At ClickUp, our "HR Goes Hard" series gets more views than most of our product demos.
 
Because even VPs need to laugh.
 
→ Thoughts?
 
I'm Chris Cunningham, I run social media marketing at ClickUp!
 
Follow me as I build this entire thing in public, right here on LinkedIn.

The moment you hit your biggest content goal, they move the goalposts.

200 million impressions? Amazing work.
300 million impressions? That's the new target.

You hit your target, and then the bar immediately raises.

Welcome to Growth Marketing.

The celebration ends.
The grind continues.

So here I am, planning our path to 300M, and I want your input.

What would YOU do in my position?

I'm Chris Cunningham, I run social media marketing at ClickUp.

Follow me as I build this entire thing in public, right here on LinkedIn.

Taplio

Chris Cunningham's Linkedin Analytics

Who is engaging with Chris

's Best Posts (last 30 days)

Want to drive more opportunities from LinkedIn?

Taplio

.css-1jgreyo{background-image:linear-gradient(284deg, rgba(39,43,72,1) 0%, rgba(33,47,183,1) 100%);color:transparent;-webkit-background-clip:text;background-clip:text;}Chris Cunningham's Linkedin Analytics

Who is engaging with Chris

's Best Posts .css-qqfgvy{font-size:var(--chakra-fontSizes-md);}(last 30 days)

Want to drive more opportunities from LinkedIn?

Chris Cunningham's Linkedin Analytics

's Best Posts (last 30 days)